Water → HCID 15079957, compound

HRID 1073848Notes

Reaction equation

HRID 1073848 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([OH:8])[CH:7]=1.[CH2:11](Br)[CH2:12][Br:13].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:13][CH2:12][CH2:11][O:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 27745595-fluoro-2-methoxyphenol

Product 1

HCID 15079957HCID 15079957, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 10.0 g of 5-fluoro-2-methoxyphenol, 52.9 g of ethylenebromide and 14.6 g of potassium carbonate in 50 ml of N,N-dimethylformamide was heated for 11 hours at 80° C. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water, dried and evaporated. The residue was chromatographed on silica gel using 50% chloroform-n-hexane as an eluent to give 11.6 g of the desired compound as a colorless oil.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica gel using 50% chloroform-n-hexane as an eluent

Sources & evidence

ORD record
ord-5139b037b59f44eda76046784919d94b
Source dataset
uspto-grants-1990_11
Patent number
US04971990

Reaction notes

Loading…